4,4,9,9-tetra-p-tolyl-4,9-dihydro-s-indaceno[1,2-b:5,6-b']dithiophene

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: 4,4,9,9-tetra-p-tolyl-4,9-dihydro-s-indaceno[1,2-b:5,6-b']dithiophene
• 英文别名: 4,9-dihydro-4,4,9,9-tetrakis(4-methylphenyl)-s-indaceno[1,2-b:5,6-b']dithiophene；9,9,18,18-Tetrakis(4-methylphenyl)-5,14-dithiapentacyclo[10.6.0.03,10.04,8.013,17]octadeca-1(12),2,4(8),6,10,13(17),15-heptaene
• 化学式: C₄₄H₃₄S₂
• 分子量: 626.886
• InChiKey: YKLQMTVONYLGLB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.3
• 重原子数：
  46
• 可旋转键数：
  4
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  56.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4,4,9,9-tetra-p-tolyl-4,9-dihydro-s-indaceno[1,2-b:5,6-b']dithiophene 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 氯仿 为溶剂， 以91%的产率得到2-bromo-4,4,9,9-tetra-p-tolyl-4,9-dihydro-s-indaceno[1,2-b:5,6-b']dithiophene
  参考文献：
  名称：

  Thiophene-fused coplanar sensitizer for dye-sensitized solar cells

  摘要：

  We have designed and synthesized a novel ladder-type heteroacene dye consisting uniquely of thiophene segments as a photosensitizer for the dye-sensitized solar cells (DSSCs). The onset of the IPCE spectrum for the dye not only reaches up to 700 nm with a high IPCE (>60%) but also a solar energy-to-electricity conversion efficiency of 2.31% is achieved. Even though the efficiency is slightly lower than those of other dyes reported previously, this work opens up a new strategy to design heteroaromatic fused photosensitizers for DSSCs. Crown Copyright (C) 2011 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.03.091
• 作为产物：
  描述：

  2,5-二溴对苯二甲酸二乙酯 在 硫酸 、 溶剂黄146 、 zinc(II) chloride 作用下， 以 四氢呋喃 为溶剂， 反应 4.5h， 生成 4,4,9,9-tetra-p-tolyl-4,9-dihydro-s-indaceno[1,2-b:5,6-b']dithiophene
  参考文献：
  名称：

  Syntheses and Structures of Novel Heteroarene-Fused Coplanar π-Conjugated Chromophores

  摘要：

  We have synthesized a series of novel coplanar chromophores in which heteroarenes, namely, thiophene, benzothiophene, and carbazole, were fused to neighboring phenylene ring(s) through intramolecular annulation via sp(3)-hybridized carbon atoms bearing two p-tolyl groups as peripheral substituents. The molecular configurations of the d-conjugated backbones were determined by X-ray crystallographic analysis; the heteroarene-fused molecular frameworks of these novel molecules exhibit nearly coplanar conformations.

  DOI：

  10.1021/ol061791y

文献信息

• High-luminescence non-doped green OLEDs based on a 9,9-diarylfluorene-terminated 2,1,3-benzothiadiazole derivative
  作者：Sung-Yu Ku、Liang-Chen Chi、Wen-Yi Hung、Shih-Wei Yang、Tsung-Cheng Tsai、Ken-Tsung Wong、Yu-Hung Chen、Chih-I Wu

  DOI：10.1039/b814082k

  日期：——

  We have prepared a highly efficient non-doped green organic light-emitting diode (OLED) incorporating a novel 9,9-diarylfluorene-terminated 2,1,3-benzothiadiazole green emitter (DFBTA), which exhibits an excellent solid state photoluminescence quantum yield (81%), and new triaryldiamines (DPAInT2, DPAInF) with high hole mobility derived from rigid and coplanar cores. The optimal device: ITO/DPAInT2/DPAInF/TCTA/DFBTA/Alq3/LiF/Al displayed impressive device characteristics, including a maximum external quantum efficiency (ηext) of 3.7% (12.9 cd A−1) and a maximum brightness at 168 000 cd m−2.

  我们研制了一种高效的非掺杂绿色有机发光二极管（OLED），其中包含新型9,9-二芳基芴端基2,1,3-苯并噻二唑绿色发射体（DFBTA），该发光体具有优异的固态光致发光量子产额（81%），以及新型三芳基二胺（DPAInT2、DPAInF），具有源自刚性共面核心的高空穴迁移率。最佳器件：ITO/DPAInT2/DPAInF/TCTA/DFBTA/Alq3/LiF/Al具有令人印象深刻的器件特性，包括3.7%的最大外部量子效率（ηext）（12.9 cd A−1）和168000 cd m−2的最大亮度。
• Distinct luminescent properties between thiophene-S-oxide and Thiophene-S, S-dioxides incorporated ladder-type molecules
  作者：Jian Cao、Shiqi Li、Hua-Chun Wang、Si-Jie Bai、Zhangyan Wang、Xiancheng Ren、Yun-Xiang Xu

  DOI：10.1016/j.dyepig.2019.108147

  日期：2020.4

  Oxidized thiophene incorporated molecules show great potential as luminescent materials. However, most works focused on thiophene-S, S-dioxides (TDO) moiety, rarely on thiophene-S-oxide (TO) incorporated molecules. Herein, TO and TDO incorporated ladder-type molecules, namely IDT2O–H and IDT4O–H, have been designed and synthesized to study their luminescent properties. Compared to IDT4O–H, IDT2O–H

  结合有氧化噻吩的分子显示出巨大的潜力，可作为发光材料。然而，大多数工作集中在噻吩-S，S-二氧化物（TDO）部分，很少涉及噻吩-S-氧化物（TO）结合的分子。在这里，已经设计并合成了TO和TDO掺入的梯形分子IDT2O–H和IDT4O–H，以研究它们的发光特性。与IDT4O–H相比，IDT2O–H不仅在溶液和薄膜状态下显示出更强的红移荧光发射，而且在薄膜状态下还显示出不同寻常的抗Kasha磷光。实验光谱和理论计算表明，来自其结构的不同能级和轨道特征对于IDT2O–H和IDT4O–H的不同发光特性至关重要。
• Tetra-aryl indacenodithiophene-based polycyclic polymers and their use
  申请人：Merck Patent GmbH

  公开号：US10270034B2

  公开（公告）日：2019-04-23

  The present invention relates to compounds comprising a tetra-aryl indacenodithiophene-based structural unit, the synthesis of such compounds as well as their use in organic electronic devices. The invention further relates to organic electronic devices comprising such compounds.

  本发明涉及包含四芳基茚并噻吩结构单元的化合物、此类化合物的合成及其在有机电子器件中的应用。本发明还涉及包含此类化合物的有机电子器件。
• SOLUBLE POLYTHIOPHENE DERIVATIVES
  申请人：Chan Shu-Hua

  公开号：US20090171048A1

  公开（公告）日：2009-07-02

  The present invention discloses a soluble polythiophene derivative containing highly coplanar repeating units. The coplanar characteristic of the TPT (thiophene-phenylene-thiophene) units improves the degree of intramolecular conjugation and intermolecular π-π interaction. The polythiophene derivative exhibits good carrier mobility and is suitable for use in optoelectronic devices such as organic thin film transistors (OTFTs), organic light-emitting diodes (OLEDs), and organic solar cells (OSCs).
• SOLUBLE POLYTHIOPHENE DERIVATIVES
  申请人：Chan Shu-Hua

  公开号：US20090299029A1

  公开（公告）日：2009-12-03

  The present invention discloses a soluble polythiophene derivative containing highly coplanar repeating units. The coplanar characteristic of the TPT (thiophene-phenylene-thiophene) units improves the degree of intramolecular conjugation and intermolecular π-π interaction. The polythiophene derivative exhibits good carrier mobility and is suitable for use in optoelectronic devices such as organic thin film transistors (OTFTs), organic light-emitting diodes (OLEDs), and organic solar cells (OSCs).